Characterization of active oxygen species under oxygen-alkali bleaching conditions
-
Tomoya Yokoyama
Abstract
The reactivities of active oxygen species toward a non-phenolic lignin model compound, 1-(3,4-dimethoxyphenyl)-1,2-ethanediol (veratryl glycol, VG), and a carbo-hydrate model compound, methyl β-D-glucopyranoside (MGP), were examined and compared under practical oxygen bleaching conditions. In this study, active oxygen species were generated in situ by subjecting a phenolic compound, 2,4,6-trimethylphenol, to oxygen oxidation to faithfully simulate practical oxygen bleaching. The results indicated that the time-dependent reaction selectivity of active oxygen species between VG and MGP, kVG(t)/kMGP(t), in the early stage of the reaction is 2.1 and 0.3–0.7 at initial pH values of 11.8 and 13.1, respectively. By comparing this value with the of hydroxyl radical obtained by Ek et al. [Holzforschung 43 (1989) 391] we conclude that the active oxygen species in the early stage of the reaction are hydroxyl radicals. The reaction selectivity at higher pH was much lower, which is explained by the fact that an oxyl anion radical, the conjugate base of the hydroxyl radical, predominantly abstracts hydrogen from aliphatic substructures. Chain-type reactions could be mainly responsible for degradation of the model compounds after the middle stage of the reaction. We suggest that the operation of chain-type reactions is not greatly dependent on the pH of the medium, but on the structure of the substrate.
References
Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B. (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution. J. Phys. Chem. Ref. Data17(2):513–520.10.1063/1.555805Suche in Google Scholar
Ek, M., Gierer, J., Jansbo, K., Reitberger, T. (1989) Study on the selectivity of bleaching with oxygen-containing species. Holzforschung43(6):391–396.10.1515/hfsg.1989.43.6.391Suche in Google Scholar
Ericsson, B., Lindgren, B.O., Theander, O. (1971) Factors influencing the carbohydrate degradation under oxygen-alkali bleaching. Svensk Papperstidn.74(22):757–765.Suche in Google Scholar
Gersmann, H.R., Bickel, A.F. (1962) Autoxidation of hindered phenols in alkaline media part 2. J. Chem. Soc.1962, 2356–2360.10.1039/jr9620002356Suche in Google Scholar
Gierer, J. (1986) Chemistry of delignification part 2: reactions of lignins during bleaching. Wood Sci. Technol.20(1):1–33.10.1007/BF00350692Suche in Google Scholar
Gierer, J. (1990a) Basic principles of bleaching part 1: cationic and radical processes. Holzforschung44(5):387–394.Suche in Google Scholar
Gierer, J. (1990b.) Basic principles of bleaching part 2: anionic processes. Holzforschung44(6):395–400.Suche in Google Scholar
Gierer, J. (1997) Formation and involvement of superoxide (O2−•/HO2•) and hydroxyl (HO•) radicals in TCF bleaching processes: a review. Holzforschung51(1):34–46.10.1515/hfsg.1997.51.1.34Suche in Google Scholar
Gierer, J., Imsgard, F. (1977) The reaction of lignins with oxygen and hydrogen peroxide in alkaline media. Svensk Papperstidn.80(16):510–518.Suche in Google Scholar
Gierer, J., Nilvebrant, N.O. (1994) Studies on the degradation of lignins by oxygen in acidic media. Holzforschung48(Suppl.):51–58.10.1515/hfsg.1994.48.s1.51Suche in Google Scholar
Gierer, J., Yang, E., Reitberger, T. (1992) The reactions of hydroxyl radicals with aromatic rings in lignins, studied with creosol and 4-methylveratrol. Holzforschung46(6):495–504.10.1515/hfsg.1992.46.6.495Suche in Google Scholar
Gierer, J., Jansbo, K., Reitberger, T. (1993) Formation of hydroxyl radicals from hydrogen peroxide and their effect on bleaching of mechanical pulps. J. Wood Chem. Technol.13(4):561–581.10.1080/02773819308020534Suche in Google Scholar
Gierer, J., Yang, E., Reitberger, T. (1994) On the significance of the superoxide radical (O2−•/HO2•) in oxidative delignification, studied with 4-t-butylsyringol and 4-t-butylguaiacol. Holzforschung48(5):405–414.10.1515/hfsg.1994.48.5.405Suche in Google Scholar
Gierer, J., Yang, E., Reitberger, T. (1996a) The reactions of chromophores of the stilbene type with hydroxyl radical (HO•) and superoxide radical (O2−•/HO2•) part 1: the cleavage of the conjugated double bond. Holzforschung50(4):342–352.10.1515/hfsg.1996.50.4.342Suche in Google Scholar
Gierer, J., Yang, E., Reitberger, T. (1996b) The reactions of chromophores of the stilbene type with hydroxyl radical (HO•) and superoxide radical (O2−•/HO2•) part 2: reactions other than cleavage of the conjugated double bond. Holzforschung50(4):353–359.10.1515/hfsg.1996.50.4.353Suche in Google Scholar
Gierer, J., Reitberger, T., Yang, E., Yoon, B.-H. (2001) Formation and involvement radicals in oxygen delignification studied by the autoxidation of lignin and carbohydrate model compounds. J. Wood Chem. Technol.21(4):313–341.10.1081/WCT-100108329Suche in Google Scholar
Guay, D.F., Cole, B.J.W., Fort Jr., R.C., Genco, J.M., Hausman, M.C. (2000) Mechanisms of oxidative degradation of carbohydrates during oxygen delignification. I. Reaction of photochemically generated hydroxyl radical with methyl β-D-glucoside. J. Wood Chem. Technol.20(3):375–394.Suche in Google Scholar
Johansson, E., Ljunggren, S. (1994) The kinetic of lignin reactions during oxygen bleaching part 4: the reactivities of different lignin model compounds and the influence of metal ions on the rate of degradation. J. Wood Chem. Technol.14(4):507–525.10.1080/02773819408003110Suche in Google Scholar
Ljunggren, S. (1986) Kinetic aspects of some lignin reactions in oxygen bleaching. J. Pulp Pap. Sci.12(2):J54–J57.Suche in Google Scholar
Ljunggren, S. (1990) The kinetic of lignin reactions during oxygen bleaching part 1: the reactivity of p,p′-dihydroxystilbene. Nord. Pulp Pap. Res. J.5(1):38–43.10.3183/npprj-1990-05-01-p038-043Suche in Google Scholar
Ljunggren, S., Johansson, E. (1990a) The kinetic of lignin reactions during oxygen bleaching part 2: the reactivity of 4,4′-dihydroxy-3,3′-dimethoxystilbene. Nord. Pulp Pap. Res. J.5(3):148–154.10.3183/npprj-1990-05-03-p148-154Suche in Google Scholar
Ljunggren, S., Johansson, E. (1990b) The kinetic of lignin reactions during oxygen bleaching part 3: the reactivity of 4-n-propylguaiacol and 4,4′-di-n-propyl-6,6′-biguaiacol. Holzforschung44(4):291–296.10.1515/hfsg.1990.44.4.291Suche in Google Scholar
Stenman, D., Carlsson, M., Jonsson, M., Reitberger, T. (2003) Reactivity of the carbonate radical anion towards carbohydrate and lignin model compounds. J. Wood Chem. Technol.23(1):47–69.Suche in Google Scholar
Sugimoto, T, Morishita, T., Matsumoto, Y., Meshitsuka, G. (2000) Effect of oxygen pressure on the oxidation of syringyl alcohol initiated by manganese(III) acetate. Holzforschung54(3):262–268.10.1515/HF.2000.044Suche in Google Scholar
Sultanov, V.S., Wallis, A.F.A. (1991) Reactivities of guaiacyl and syringyl lignin model phenols towards oxidation with oxygen-alkali. J. Wood Chem. Technol.11(3):291–305.10.1080/02773819108050276Suche in Google Scholar
Yasumoto, M., Matsumoto, Y., Ishizu, A. (1996) The role of peroxide species in the carbohydrate degradation during oxygen bleaching part 1: factors influencing the reaction selectivity between carbohydrate and lignin model compounds. J. Wood Chem. Technol.16(1):95–107.10.1080/02773819608545785Suche in Google Scholar
Yokoyama, T., Matsumoto, Y., Yasumoto, M., Meshitsuka, G. (1996) The role of peroxide species in the carbohydrate degradation during oxygen bleaching part 2: effect of oxygen pressure on the degradation of lignin and carbohydrate model compounds and on the reaction selectivity. J. Pulp Pap. Sci.22(5):J151–J154.Suche in Google Scholar
Yokoyama, T., Maekawa, I., Matsumoto, Y., Meshitsuka, G. (1998) Reaction selectivity of active oxygen species produced by an oxygen-alkali oxidation of a phenolic compound. J. Wood Sci.44(5):421–422.10.1007/BF01130459Suche in Google Scholar
Yokoyama, T., Matsumoto, Y., Meshitsuka, G. (1999a.) The role of peroxide species in the carbohydrate degradation during oxygen bleaching part 3: effect of metal ions on the reaction selectivity between lignin and carbohydrate model compounds. J. Pulp Pap. Sci.25(2):42–46.Suche in Google Scholar
Yokoyama, T., Matsumoto, Y., Meshitsuka, G. (1999b) Reaction selectivity of active oxygen species in oxygen-alkali bleaching. J. Wood Chem. Technol.19(3):187–202.10.1080/02773819909349607Suche in Google Scholar
© by Walter de Gruyter Berlin New York
Artikel in diesem Heft
- Molecular dynamics study of lignin constituents in water
- Oxidative cellulose degradation by cellobiose dehydrogenase from Phanerochaete chrysosporium: A model compound study
- Characterization of active oxygen species under oxygen-alkali bleaching conditions
- Erythro/threo ratio of β-O-4-5 structures as an important structural characteristic of lignin. Part 4: Variation in the erythro/threo ratio in softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio
- Stereoisomers of 3,3′-dimethoxy-4,4′-stilbenequinone
- Liquefaction of CCA-treated wood and elimination of metals from the solvent by precipitation
- Condensed tannins from steamed Acacia mearnsii bark
- Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood
- Direct measurement of strain distribution along a wood bond line. Part 1: Shear strain concentration in a lap joint specimen by means of electronic speckle pattern interferometry
- Direct measurement of strain distribution along a wood bond line. Part 2: Effects of adhesive penetration on strain distribution
- Rate-independent mechanical behavior of biaxially stressed wood: Experimental observations and constitutive modeling as an orthotropic two-surface elasto-plastic material
- Characterization of sugar maple wood-polymer composites: Monomer retention and polymer retention
- New insights into wood and cement interaction
- Wood-water sorption isotherm prediction with artificial neural networks: A preliminary study
- Hygroscopicity of resorcinol-formaldehyde resin and aqueous vinyl polymer-isocyanate resin in high humidity
- Modelling anisotropic maturation strains in wood in relation to fibre boundary conditions, microstructure and maturation kinetics
- Properties of chemically and mechanically isolated fibres of spruce (Picea abies [L.] Karst.). Part 3: Mechanical characterisation
- Resistance of thermo-hygro-mechanically densified wood to colonisation and degradation by brown-rot fungi
- Microbial colonizers of freshly sawn yellow-poplar (Liriodendron tulipifera L.) lumber in two seasons. Part 3: Yeasts
- Efficacy of a copper(II)/oxine copper wood preservative mixture after 69 months of outdoor ground-contact exposure and a proposed mechanism to explain the observed synergism
- Differentiation of indoor wood decay fungi with MALDI-TOF mass spectrometry
- Horst H. Nimz celebrates his 75th birthday on April, 21st, 2005
- Erratum
Artikel in diesem Heft
- Molecular dynamics study of lignin constituents in water
- Oxidative cellulose degradation by cellobiose dehydrogenase from Phanerochaete chrysosporium: A model compound study
- Characterization of active oxygen species under oxygen-alkali bleaching conditions
- Erythro/threo ratio of β-O-4-5 structures as an important structural characteristic of lignin. Part 4: Variation in the erythro/threo ratio in softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio
- Stereoisomers of 3,3′-dimethoxy-4,4′-stilbenequinone
- Liquefaction of CCA-treated wood and elimination of metals from the solvent by precipitation
- Condensed tannins from steamed Acacia mearnsii bark
- Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood
- Direct measurement of strain distribution along a wood bond line. Part 1: Shear strain concentration in a lap joint specimen by means of electronic speckle pattern interferometry
- Direct measurement of strain distribution along a wood bond line. Part 2: Effects of adhesive penetration on strain distribution
- Rate-independent mechanical behavior of biaxially stressed wood: Experimental observations and constitutive modeling as an orthotropic two-surface elasto-plastic material
- Characterization of sugar maple wood-polymer composites: Monomer retention and polymer retention
- New insights into wood and cement interaction
- Wood-water sorption isotherm prediction with artificial neural networks: A preliminary study
- Hygroscopicity of resorcinol-formaldehyde resin and aqueous vinyl polymer-isocyanate resin in high humidity
- Modelling anisotropic maturation strains in wood in relation to fibre boundary conditions, microstructure and maturation kinetics
- Properties of chemically and mechanically isolated fibres of spruce (Picea abies [L.] Karst.). Part 3: Mechanical characterisation
- Resistance of thermo-hygro-mechanically densified wood to colonisation and degradation by brown-rot fungi
- Microbial colonizers of freshly sawn yellow-poplar (Liriodendron tulipifera L.) lumber in two seasons. Part 3: Yeasts
- Efficacy of a copper(II)/oxine copper wood preservative mixture after 69 months of outdoor ground-contact exposure and a proposed mechanism to explain the observed synergism
- Differentiation of indoor wood decay fungi with MALDI-TOF mass spectrometry
- Horst H. Nimz celebrates his 75th birthday on April, 21st, 2005
- Erratum
